Synthesis, characterization of metal-free, metallophthalocyanines and catalytic activity of cobalt phthalocyanine in cyclohexene oxidation

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• 作者：Serpil G?k?e ; Ece Tu?ba Saka ; Zekeriya B?y?kl?o?lu ; Halit Kantekin
• 关键词：Phthalocyanine ; Metal-free ; Cobalt ; Cyclohexene oxidation ; Oxidant ; tert-Butylhydroperoxide
• 刊名：Synthetic Metals
• 出版年：2013
• 出版时间：15 July, 2013
• 年：2013
• 卷：176
• 期：Complete
• 页码：108-115
• 全文大小：1424 K

文摘

In this work, the new phthalonitrile derivative 3 bearing 4-pentylphenol 1, metal-free phthalocyanine 4, metallophthalocyanines 5 and 6 have been synthesized. Metal free phthalocyanine 4 and metallophthalocyanines 5 and 6 bearing four 4-(4-pentylphenoxy) groups on the periphery have prepared by cyclotetramerization of a new precursor, namely 4-(4-pentylphenoxy)phthalonitrile 3 in the presence of the corresponding divalent metal salts [Zn(II), Co(II)]. The new compounds have been characterized by IR, ¹H NMR, ¹³C NMR and MS spectra data. The new cobalt phthalocyanine 6 has tested as a catalyst for the oxidation of cyclohexene with different oxidants, such as tert-butylhydroperoxide (TBHP), m-chloroperoxybenzoic acid (m-CPBA) and hydrogen peroxide (H₂O₂), in organic solvent. It is seen that complex 6 can selectively oxidize cyclohexene to give 2-cyclohexen-one as major product, 2-cyclohexen-ol and cyclohexene oxide as minor product. Finally, because of the minimal destruction of the catalyst, higher selectivity and conversion, TBHP has found to be best oxidant.